A historic building with classical architecture, a traffic light, and a yellow taxi.

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Check availability on Pittsfield Family Hotels

Tonight
Oct 9 - Oct 10
Tomorrow
Oct 10 - Oct 11
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Pittsfield family-friendly hotels

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

1. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
NT$4,084
NT$4,562 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
A bookshelf with various books and games, a 'RELAX' sign, and two red pillows on a bench.
A building entrance with a large planter with purple flowers and a small tree.
A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.
A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

2. Hotel On North

Hotel On North
Pittsfield
NT$4,283
NT$4,784 total
includes taxes & fees
Nov 1 - Nov 2
Hotel On North
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

3. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
  • Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Center.
NT$3,162
NT$3,532 total
includes taxes & fees
Nov 9 - Nov 10
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.
A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.
A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

4. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
  • Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
NT$2,986
NT$3,335 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Plus Berkshire Hills Inn & Suites
A room with a pool table, arcade games, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
NT$2,738
NT$3,772 total
includes taxes & fees
Nov 9 - Nov 10
Berkshire Mountain Lodge
Room
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
An indoor swimming pool with clear pool rules signage, multiple seating areas, and a view of the outdoors through large windows.
A bathroom with a large mirror, a sink, and a towel rack.

6. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
  • Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
NT$3,130
NT$3,496 total
includes taxes & fees
Nov 6 - Nov 7
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A hotel room with two beds, a nightstand with a lamp, and a window with curtains.
A bathroom with a toilet, shower, and bathtub.
A compact living space with a kitchenette, a dining area, and a sofa.

7. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
NT$3,162
NT$3,532 total
includes taxes & fees
Oct 14 - Oct 15
The Central Downtown Inn & Suites
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.
A dining area with wooden tables and chairs, a television, and a door with a sign.
A hotel room with a fitness center including a weight machine, an elliptical, and a treadmill.
A bathroom with a bathtub, a sink, and a mirror.

8. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
NT$1,980
NT$2,212 total
includes taxes & fees
Oct 22 - Oct 23
FairBridge Inn Express
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.

9. The Yankee Inn

The Yankee Inn
Lenox
  • Family escape with indoor and outdoor pools—enjoy year-round swimming plus convenient ski access at Bousquet Ski Area.
NT$3,386
NT$3,782 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A rectangular swimming pool with a white metal fence, surrounded by white lounge chairs and a blue umbrella.
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
A bathroom with a white sink, mirror, and toilet.

10. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Family escape with outdoor pool and ski resort access—kids love the convenient location and amenities for all ages.
NT$2,519
NT$2,814 total
includes taxes & fees
Oct 22 - Oct 23
Howard Johnson by Wyndham Lenox
View all properties

Choose what matters most at family-friendly hotels in Pittsfield

Pool
Breakfast included
All-inclusive
4 stars
5 stars

Top Pittsfield Hotel Reviews

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Room was spacious and clean"
James 1-night trip
Posted 3 hours ago
Best Western Plus Berkshire Hills Inn & Suites
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

8/10 Good
"It was fine but not remarkable"
Edgar 2-night trip
Posted 3 hours ago
Comfort Inn & Suites East Greenbush - Albany
Hotel On North

Hotel On North

10/10 Excellent
"The hotel location is very good with convenient parking in the rear. We liked the large room. Lighting was a little dim in our room but it was very comfortable and spacious. The staff were very polite and helpful."
Julia 3-night trip
Posted 3 hours ago
Hotel On North
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We were surprised by the space that we got!! The lay out of the suite was so pleasant. We enjoyed the stay tremendously."
Susanna 1-night trip
Posted 4 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Although it's an older hotel, it's well maintained.Clean and updated also very friendly staff."
Marti 1-night trip
Posted 5 hours ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Property was clean, staff was knowledgeable and cordial. Parking was very easy."
Julia 1-night trip
Posted 6 hours ago
Hotel Downstreet, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"
Joanne 1-night trip
Posted 3 days ago
The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."
Leslie 2-night trip
Posted 4 days ago
Quality Inn Great Barrington
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

8/10 Good
"The staff were helpful and the room was clean. Overall the experience was good"
tuhin 1-night trip
Posted 5 days ago
The Central Downtown Inn & Suites

Frequently asked questions

What's Pittsfield like for family-friendly vacations?
If you've been thinking about a trip with your kids, the historic destination of Pittsfield is a good choice. The biking trails, entertainment, and lake views are just some of the things that make this the perfect spot for family trips. Take to the air and fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest airport, or Hudson, NY (HCC-Columbia County), which is located 25.7 mi (41.4 km) from the city center.
What's the best hotel when traveling with kids to Pittsfield?
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG is a hotel with an indoor pool and free parking, and it's a top choice on Expedia for families. Other choices for your family trip include Best Western Plus Berkshire Hills Inn & Suites and Holiday Inn & Suites Pittsfield-Berkshires by IHG.
When's the best time to book a family-friendly vacation in Pittsfield?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's there to see and do with your family in Pittsfield?
Colonial Theater, Bousquet Ski Area, and Barrington Stage Company are interesting attractions you and your family will enjoy exploring while you are staying in Pittsfield. Make sure you have lots of time for activities like Guido's Marketplace and Berkshire Athenaeum.
What's the best way for us to get around Pittsfield?
To see more of the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station. Pittsfield might not have many public transit options so consider renting a car to explore more.

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